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7. Carbonyl Iron Powder: A Reagent for Nitro Group Reductions under Aqueous Micellar Catalysis Conditions

Author

Lee, Nicholas R., Bikovtseva, Agata A., Cortes-Clerget, Margery, Gallou, Fabrice, and Lipshutz, Bruce H.

Abstract

An especially mild, safe, efficient, and environmentally responsible reduction of aromatic and heteroaromatic nitro-group-containing educts is reported that utilizes very inexpensive carbonyl iron powder (CIP), a highly active commercial grade of iron powder. These reductions are conducted in the presence of nanomicelles composed of TPGS-750-M in water, a recyclable aqueous micellar reaction medium. This new technology also shows broad scope and scalability and presents opportunities for multistep one-pot sequences involving this reducing agent.

Published
2024
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14. Effects of Co-solvents on Reactions Run under Micellar Catalysis Conditions.

Author

Gabriel, Christopher M., Lee, Nicholas R., Bigorne, Florence, Klumphu, Piyatida, Parmentier, Michael, Gallou, Fabrice, and Lipshutz, Bruce H.

Subjects
*MICELLAR catalysis, *ORGANIC solvents, *MICELLES, *CHEMICAL reactions, *AQUEOUS solutions
Abstract

The impact of varying percentages of an organic solvent added to reactions run in aqueous nanomicelles as the reaction medium has been investigated. Issues such as rates of reaction, percent conversion, and yield, as well as various practical aspects (e.g., effect on stirring, etc.), are discussed, leading to an operationally simple method for the general improvement of potentially problematic systems across a broad range of reaction types, in particular for reactions run at scale. [ABSTRACT FROM AUTHOR]

Published
2017
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15. B-Alkyl sp 3 -sp 2 Suzuki-Miyaura Couplings under Mild Aqueous Micellar Conditions.

Author

Lee NR, Linstadt RTH, Gloisten DJ, Gallou F, and Lipshutz BH

Abstract

Use of B-sp 3 -alkyl reagents for Suzuki-Miyaura couplings under aqueous micellar catalysis conditions is reported. Studies as to substrate scope, use in a four-step one-pot sequence, and reaction medium recycling exemplify the synthetic utility of this technology. OBBD ( B-alkyl-9-oxa-10-borabicyclo[3.3.2]decane) derivatives are easily made and utilized for couplings under mild conditions. Comparisons were also made between OBBD and 9-BBN ( B-alkyl-9-borabicyclo[3.3.1]nonane) derivatives as reaction partners.

Published
2018
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